


One Goes to Stiles

by Cathbadh



Category: Teen Wolf (TV)
Genre: Anal, Anal Fisting, Cuddles, Cuddling, Fisting, Friends With Benefits, M/M, Platonic Relationship, Platonic Sex, Skittles, platonic sex partner
Language: English
Status: Completed
Published: 2014-07-10
Updated: 2014-07-10
Packaged: 2018-02-08 05:50:13
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 3,631
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/1929036
Author URL: https://archiveofourown.org/users/Cathbadh/pseuds/Cathbadh
Summary: <blockquote class="userstuff">
              <p>Scott had it all planned out with Allison: she'd get the strap-on, he'd get a lot of lube (one that smelled nice, and, of course, functioned well), they'd get together, and.... Then they broke up. Scott was heartsick, of course, but he was also disappointed: he never to go try anal! So what does one do? Scott went to Stiles.</p>
            </blockquote>





	One Goes to Stiles

Scott had it all planned out with Allison: she'd get the strap-on, he'd get a lot of lube (one that smelled nice, and, of course, functioned well), they'd get together, and.... Then they broke up. Scott was heartsick, of course, but he was also disappointed: he never to go try anal! So what does one do? Scott went to Stiles.

“You want me to what?” Stiles stared at Scott, taken aback.

Damn, how does he explain this? “Um, see, Allison and I, we wanted to try anal. On me. But. . .”

Stiles interrupted. “I thought you weren't listening when I asked if gay guys found me attractive! Sure, why not, I'll do it. Just for you buddy!” Stiles pat Scott on the back and smiled.

Besides the wink that made Scott worry if Stiles thought this was more than it really was, that wasn't too bad, well, no, that was really hard actually. 

“Let's start tonight! Your mom doesn't get back until late, right?” 

“Oh, yeah, good point.”

“Yeah you don't want to wait, right? You're really looking forward to this, right?”

“Yeah, I am, actually.” 

“Great! I'll be there after school!”

“Yeah, see you then!” Scott turned, and hurried to get to economics in time.

 

Scott returned home to find Stiles already in his room. “I get the feeling you're just as excited about this as I am.” Scott mused. He wondered if Stiles was crushing on him. He didn't want to hurt his best friend. Someone he loved dearly—platonically—and it seemed Stiles loved him back. Enough to. . . help him with his sex life? 

“Yeah! You know I had gotten this book back when I was first curious about the subject,” Stiles held up the book he was holding to show Scott, who read “The Ultimate Guide to Prostate Pleasure” on the cover and raised his eyebrows. Stiles came prepared, that certainly can be said.

Stiles continued: “and now that you're interested in it, I brought it to you! It's a bit basic for me now.” This was basic to Stiles now? How much is there to know?

“Well, this is all very kind of you, but. . .” Scott hesitated. 

“Oh, yeah, you're nervous? Don't worry, I get it! I was nervous too when I started to experiment!”

Wait, started to experiment? Has he continued? What sexual theories has Stiles discovered? Scott opened his mouth. “Experiment?”

“Don't worry bro, I'll go nice and slow with you, and you tell me what you think is good to start with, okay? Nothing to worry about!”

“What did you find out about yourself?” Scott wondered how much pleasure one could have.

Stiles nearly yelled, “It feels amazing!” Then added, “Also, I think I'm bisexual. Well, pretty sure. Positive, actually.” Stiles's eyes went wide. “Oh! No, I'm not crushing on you. Buddy. Platonic buddy.” Stiles smacked Scott's arm.

“Oh!” Scott felt a little better, but what was this other feeling? Disappointment? “Um, oh.”

“Aw, are you disappointed? Buddy!” Stiles patted Scott on the shoulder and smiled. “Well I am flattered that this town's True Alpha is disappointed that I wasn't crushing on him! Damn, you're a sweet kid.” Stiles shook his head, put his hands on his hips, and smiled brighter at Scott. “So let's get started!”

Stiles sat on the floor and opened the book again. “Okay, let's start with the basics. Do you know what the prostate even is? You're not failing biology again, are you?”

Getting over himself, Scott tried to remember about the prostate without blushing too much. “Um, it's the glad that creates ejaculate during orgasm.” 

“Right you are!” Stiles smiled again. “Okay, so you're not at the total ditz level, good, good. Okay, next, while the prostate isn't the sole reason people want things up their butt, it is a big reason. Orgasmic reason.” Stiles trailed off for a second. Scott poked him. “Sorry, remembering how good it feels can be distracting. Anyway, massaging it can really make your orgasms,” Stiles gesticulated haphazardly and his voice went up an octave, holding the last syllable, “awesome!”

Scott nodded. “Yeah, that's one thing Allison and I wanted to try. I'm not sure how I'm supposed to get anything up there, though.”

“Lube, dude. Lube.” Stiles looked at Scott like he was supposed to know this already, and Scott did.

“No, I know that, but, it's so tight.”

“You go slow! It's not a race, dude, well, I mean, not for most people. Anyway, you'll find in this book that going slowly helps you, well, get excited faster. I've found that for myself, too.” 

Scott blushed.

“Aww, dude! It'll be fine! We don't have to try anything today. Just read through this book and then we'll start tomorrow.”

“Okay.” Scott accepted the book from Stiles, who continued to smile at Scott's blush. 

“You're gonna love this! Now, I assume you have lube since you already knew about that, but do you have condoms? You're my friend and all, man, but I don't want to touch your actual shit.”

“Oh, yeah, I have a few, but I'm almost out.” Scott scratched behind his ear.

“That's my boy! Alright I'll get some more on my way home.”

“Wait, why are we using condoms? Why not gloves?” 

“Condoms are good for using one finger, which I figured we'd start with, but gloves are good too. I just, you know, figured you'd already have condoms, but not gloves.”

“My mom's a nurse, of course we have gloves.”

“Oh, right.” Stiles looked thoughtful. “You wanna try now, then? You've got lube, right? I bet your mom would too.”

Scott looked appalled. “Yeah, we'll just go up to her, 'Hey mom, you got gloves and lubricant? Stiles and I want to try something.' I'm sure she'll think we were up to something completely innocent!”

“Hey, I use gloves and lubricant all the time!” Scott raised his eyebrows. “Oh, right. But it's totally for an innocent purpose!”

“And exploring sex with your best friend is innocent?”

“I guess it depends on what you would call innocent.”

“Wouldn't that include sex? What do you think is innocent?” Scott repeated, sceptically.

“Sex with... your best friend! Sex with your best friend is about experimentation, discovery, and learning about each other, forming a closer bond of good and wholesome friendship.” Stiles nodded patiently.

“And if you were best friends with Jackson?”

“That would be the most despicable thing ever.”

“Did you call Lydia despicable?”

“Hey, don't go there or I'll hit your mean wolfie ass.”

Scott laughed with Stiles. Despite how awkward he had felt about this at the beginning, Scott felt more relaxed now. Something about Stiles's bad jokes always helped him relax, somehow.

“Alright, let's do this, but don't take it seriously.”

“Scott. Me? Take this seriously? Ptah, when do I ever take anything seriously?”

Scott started to consider that, then decided better. “I just mean, you know, don't sound too clinical. That'll just make me feel awkward.”

“Don't worry, buddy, I'll make this fun for you.” Stiles smiled at his friend. 

Scott left and returned with a big, fluffy, brown towel. He laid the towel down on the bed, and stripped.

“Wait, hold on, I realized I should ask, have you pooped yet today?”

Scott's eyes went wide. “Yes? What kind of a question is that?”

“Dude whoa. If I'm going to finger you, it's best if there's no poop in there, right? You don't want too many things hidden away up there, right?”

Scott realized he was being silly. He didn't know about this, Stiles did. “Right, um, I went earlier today, yes, but can't you use a euphemism?”

“Dude, Scott, I don't know the euphemism for everything, first off, Jeez, second, what's the big deal? I'm not your mother, am I?” Stiles face went into a fake smile. “'Oh son, I'm wondering if you've had bowel movements today, okay honey, thank you.'” Stiles faced relaxed into bemused bewilderment. “What kind of relationship do you two even have?” Stiles rolled his eyes before Scott could respond. “Never mind.”

Scott paused for a moment. “Maybe we should wait until tomorrow.”

“Scott, did you read the book? Multiple. Orgasms. Prostate! Pleasure!” Stiles opened his arms wide. “Are you ready now?”

“Of course I haven't read the book yet, you just gave it to me.”

“Well hurry up!” 

Scott blushed. Just. . . Stiles. . . sometimes you need to shut up. “I don't think I'm going to be ready tonight. I. . . I want to, but. . .”

Stiles understood. “Sure thing, buddy.” Stiles looked Scott over, wondering what would make Scott more comfortable. “Want to cuddle? Might help you relax.”

“Cuddle?” Not what Scott expected.

“Yep!” Stiles smiled bright, and Scott couldn't say no. 

“Do we have to call it cuddling?”

“You prefer the phrase 'sleeping together'?”

“Uh.” Scott changed his mind. “Cuddling is fine!”

They spent the rest of the day working on homework, Stiles making sure Scott wasn't falling behind again. When Scott's mom returned home, she agreed that Stiles could stay the night.

“Do you need a cot or did you bring a sleeping bag?”

“He has a sleeping bag!” Scott blurted urgently. “We're going to bed, don't bug us!” Scott dragged Stiles into his room and shut the door.

“Your poor mom. Never gets to know what you're up to.”

“Shut up and cuddle me.”

“Alright, my boy! Let's do this.” Stiles rubbed his hands together impatiently and grinned mischievously.

“You make it sound so subversive.”

“Yes, we doom society with our cuddling!”

Scott raised an eyebrow. “I said to cuddle me, but also to shut up.”

“Oh right. Doing that.” Stiles showed his goofy grin.

Scott got in bed first, then held the covers open. Stiles got in and sighed dramatically. “Alright, my boy, you ready?”

“Do you want the inside or outside spoon?”

“What are we, kitchenware?” Scott glared back. “I'll take the outside spoon. But what if I were a fork?” Scott hit Stiles in the arm. 

“Shut up and go to sleep. You're warm and. . . cozy.” Stiles smiled at that. He liked Scott relaxing in his arms, and soon they both fell to sleep easily.

 

The next morning found Stiles drooling on Scott shoulder, and Scott very confused how his shoulder got wet. He sat up slowly, made a face at his shoulder after realization dawned, then gently woke Stiles awake.

“Hey there, shoulder slobberer” Scott said.

Stiles yawned. “Hi yourself. Did you sleep well? You're very comfortable, especially your shoulder. Did you know that? I dreamed you mated with a kangaroo. I didn't know werewolves could do that with their tongues.” Stiles yawned again.

Scott opened his mouth to answer, then thought better of it and motioned to Stiles to let him out of bed. 

 

They returned from school, Stiles with fresh clothes.

“You ready this time?”

“Yeah, let's try it.” Scott put his pouty, determined face on. Stiles would have made fun of him but decided against it. 

“Alright. Why don't you go down on all fours, that'll give me good access and you can rest your face on your pillow if you need.”

“You realize I'm not actually a wolf, right?” 

Scott laid the towel on his bed, took his clothes off, and got in position. Stiles ignored Scott's comment, put on gloves, and lubed them up. “If you get cold, let me know, and we can put another towel on your back. Now I'm gonna just massage around your hole.”

Stiles rubbed his thumb around Scott's hole, and tickled the taint with his index finger. “How does that feel?”

“Weird.” Scott paused. “Relaxing though.” 

A while later, Stiles went to the next step. “I'm going to put my finger in. Ready?”

“Um, yeah.”

Stiles slowly slid his index finger in. Scott breathed slowly. “How's that feel, buddy?” Scott nodded, and Stiles began a slow and simple in-and-out rhythm. He added another finger after confirming Scott's readiness for more, and smiled at Scott's moan.

“Yeah it relaxes you, doesn't it?” Scott dropped his face to the pillow and began to pant ever so slightly. He felt Stiles's fingers wiggling inside him, and they found his prostate. Stiles's warm voice came in through to his mental cloud. “I'm gonna start really massaging your prostate, make you feel good. Let me know if you want me to stop.”

With the slow and steady rhythm on that spot, a warm glow began to shine on Scott's crotch. The warmth spread slowly, and Scott widened his legs at the beckoning call of bliss. Scott moaned, at once demanding and grateful.

“I hear yah!” Stiles smile widened and he began to quicken his pace, scissoring his fingers to rub the source of Scott's pleasure in a new way. Scott groaned again. Each time Stiles's fingers did a new pattern—scissoring, circles, in-and-out with each finger alternating, both in-and-out each finger together, more circles, alternating finger circles, then scissoring again—Scott's groans grew louder and more demanding, less grateful, and Stiles's grin grew, pleased at himself.

“Another finger?” Stiles's voice teased Scott.

“Yes! Oh please, yes!” Scott enjoyed the fuck out of these fingers. The third finger entered, and Scott barely registered the extra stretch in his ass, distracted by the new ways Stiles began to play with the shining spot of joy within his sensuous ass. Stiles stroked, pressed, tickled, tantalized, manipulated, stimulated Scott's glowing spot inside. Scott's moans grew and grew until something wonderful happened. The warmth of orgasm began, grew, and spread all over and inside Scott, warming totally with pleasure. He rubbed his head into the pillow, breathing steady and happy. Stiles's rhythms stopped registering as his P-gasm continued, and Scott's moans grew less demanding, more grateful. After another minute, the bliss subsided. To his surprise, though, he was hornier than ever.

Scott, confused, asked “Wait, did I come?”

“I think you did!” Stiles grinned, pleased with himself. 

“Where's the semen? I don't see any wet spots on the towel.”

“Usually with P-spot-gasms, you don't really ejaculate. That's how you can get more than one orgasm! You do have a lot of pre-cum though. I can see it glisten. Want to keep it up?” 

“I never knew this was possible. . .” Scott trailed off, stunned. “So what're you waiting for? Do me again!”

“Oh believe me. I'm just getting started!” With a cackle, Stiles began moving his fingers inside Scott with gusto.

 

A few more days of this P-spot pleasuring by Stiles, Stiles wanted—no, needed—some reciprocation. 

“So, um, you know how I've made your wolfieness cum fifteen times in the past three days?”

“Stiles-what-the-hell-this-is-chemistry-class-SHUT-UP!” Scott hissed back.

“I want you to do me, too. Like I said, it's much easier with another person.”

“Okay-whatever-you-want-just-SHUT-UP!” Scott looked around, horrified. Only Lydia, sitting nearby, showed any sign of noticing his panic, raising an unimpressed eyebrow. Stiles, though, smiled wide and bright.

 

That afternoon, Scott's mom yet again taking an afternoon shift, Scott and Stiles prepared themselves on the bed. Stiles, this time, with his pants off.

Scott hesitated a little. “So, I just start by massaging around your hole a little?”

“Scott you can skip that, just go in slowly. I do this to myself a bit. Well, more than a bit. Okay, so a lot. Anyway, just start with two fingers.”

Scott pushed two fingers against Stiles's hole. “You sure?”

“Yeah, just go for it! I'll tell you what I want.”

“Okay. . .” Scott pushed his fingers in, feeling Stiles's warmth around his fingers. Stiles's breathed steadily.

“M-m-m. Now add another finger.”

“Already?” Scott's face crunched up. “How can you do that so fast? I'm a wolf and it took me at least thirty minutes.”

“I told you, I like to do this myself, so I've already stretched my hole a bit. But the angle is all wrong for my hand, so I can't get enough.” Stiles would have rolled his eyes if he didn't enjoy Scott's fingers so much. “Now add more fingers, please!”

“Okay, here you go.” Scott slowly pushed in his third finger.

“Ohhh, Scott that feels so good!” Stiles immediately started to pant. “Yeah, stretch that hole, oh you feel so good, yeah move in there!”

Scott, confused, stopped and asked: “Wait, you like the stretch?”

“Yes, I like it! Now stretch more, gently though, don't hurt my non-supernatural, ordinary butt-hole.”

Scott began again, slowly, trying to widen Stiles hole with his three fingers. Stiles's vocals went right back to work, panting and moaning “oh yes, oh god, more, yeah stretch it, stretch my hole, yeah Scotty do it, more please God please more, yes yes yes yes!!”

Scott couldn't help but smile at his friend in such bliss. Stiles began to stroke himself and, as he came onto the towel, his hole clenched, and Scott struggled with his hand. Stiles collapsed, and Scott removed his fingers and wiped them on the towel. Soon, Stiles fell asleep, thoroughly relaxed. Scott tucked him in, and the two friends again cuddled through the night.

 

The next day, Stiles woke up feeling more cozy than ever, wrapped in his friend's arms. As he stirred awake, he realized what happened. 

“Oh shit Scott, I'm so sorry, I didn't mean to pass out like that!”

Scott smiled at him. “It's cool! That's what friends are for.” Scott patted Stiles's shoulder, and they prepared for school. 

 

As the days turned into weeks, Scott and Stiles kept up their ass-play, Stiles first massaging Scott's insides until he comes—usually five times, not bad for a wolf—then Scott stretching Stiles hole until Stiles cums and they pass out, holding each other as they sleep. They began to study with maximum efficiency, getting ready for bed first as fast as they could, knowing they exhaust themselves, especially Stiles. They meanwhile kept Mellisa's curiosity as to their afternoon activities at bay with a story of an intense history project that made Stiles very sleepy. 

“Yeah, something about reading books on Vlad Drakul makes Stiles really sleepy.”

“Drakul? That sounds like Dracula.” Mellisa looked interested. 

“Oh, yeah, that's the person Dracula comes from. He would impale people on wooden stakes if they rebelled against his rule.

Now she looked at her son quizzically. “Why would something that horrifying be sleep-inducing?”

“Uh, I don't know! Maybe all this werewolf business made Stiles think this is...” Scott paused thinking for the right word.

“boring in comparison?” Melissa scrunched her face in skepticism. 

“I don't know, mom! But he's passed out, now.”

“Why did you take his shirt off?”

“Oh.” Scott looked at his friend, realizing he forgot that vital detail. “I didn't take it off, he did.”

“Why would he do that?”

“Maybe he just sleeps that way and unconsciously took it off?” Scott shrugged at his mom. “I dunno, I sort of stopped trying to explain Stiles a while ago.”

Mellisa pondered this. “That's a wise thought.” She turned and left her son's best friend in her son's care.

 

One day, Stiles wanted more than Scott's fingers could give. Already, they had gotten to four fingers, but Stiles wanted more. “Put your whole hand in me!”

“My whole hand? Is that even possible?” Scott frowned at his friend.

“Yeah, I looked it up online. It's called 'fisting,'” Stiles said matter of factly.

Scott had three fingers in Stiles. He pushed them all in again, then added a fourth. Stiles breathed long, slow, and deep, focused on relaxing his hole. After a few minutes of thrusting, Scott pushed his four fingers in past his knuckles, eliciting a pleased grown from Stiles. “My thumb's about to go in, are you sure you're ready for this?”

“Yeah, yeah I am.” Stiles breathed deep and deliberately. “Go slow!” he reminded.

“Of course.” Scott then began to breach with his thumb. Stiles kept up his breathing, focusing on letting more in his ass. The endorphins began to take off, lifting Stiles high on his mental cloud. Stiles kept up his breathing, and groaned with each knuckle of Scott's thumb.

“I think this is my hand at its widest, pressing on your hole.”

“Just hold it there, this feels wonderful,” Stiles said in a dreamy voice. He could feel the wide stretch of his ass, feel Scott's thumb's knuckle on the lip of his hole. Stiles dreamy breathing continued a few minutes, until Stiles was ready for the next step. “Okay, start to twist it around a little, then in and out, just like how we got here.”

Scott complied, Stiles moaned. A few minutes of this slow moving, Stiles asked for the whole hand inside, all the way. Scott pulled out a bit, then rolled his hand up, squirted on another refreshment of lube, and pushed in, slow and sure. Knuckle after knuckle disappeared inside Stiles's hole, and Stiles groaned with each inch of Scott's hand. Scott got to the widest part of his hand, and Stiles panted like a champ, his dick hard, dark, and dripping. Scott pushed in more, and Stiles felt himself fill up, and the stretch of his ass diminished. “Oh, Lord!” Stiles nearly spilled tears of joy. Instead, his cock dribbled drops of bliss. Scott twisted his forearm, and began to pull out. Stiles panting intensified the more the his hole stretched. At the maximum, he begged “Jerk me! Leave your one hand, and jerk me off with your other, please!” Scott complied. It didn't take long for a burst of warm, creamy liquid to escape from Stiles's cock. After Scott stroked what he could from Stiles, he slowly withdrew his hand.

“Okay, I think that's it for me. I'm worn out,” Stiles whispered.

“Shhh, go to sleep. I'll wipe you down and tuck you in." Stiles rolled over, and soon Scott pulled himself in bed and wrapped his arm around his best friend.

**Author's Note:**

> My second fic! Please leave suggestions/comments/whatever if you feel like it.
> 
> Also, this fic has inspired me to write a much longer, bigger fic (probably not sexier because this one was basically pure sex with some setup, also the next will have scary creatures that kill, and I think you're in the minority if that turns you on?), because what if Derek finds out??? Also, what if I tried to include plot??? Jealous!derek will be fun to write, too. "'Oh, skinny, defenseless Stiles, why can't I put my hand up your bum?' he coos softly in the moonlight." So if that tickles your fancy, I've started writing it (starting with sex, because why not?). I haven't done a big fic like that before, though, so bear with me as I figure it out.


End file.
